SE406198B - METHOD OF PREPARING 6- (ALFA-AMINOBENSYL-ALFA-PENICILLOYLAMINO) -CAPRONIC ACID - Google Patents
METHOD OF PREPARING 6- (ALFA-AMINOBENSYL-ALFA-PENICILLOYLAMINO) -CAPRONIC ACIDInfo
- Publication number
- SE406198B SE406198B SE7203125A SE312572A SE406198B SE 406198 B SE406198 B SE 406198B SE 7203125 A SE7203125 A SE 7203125A SE 312572 A SE312572 A SE 312572A SE 406198 B SE406198 B SE 406198B
- Authority
- SE
- Sweden
- Prior art keywords
- alfa
- penicilloylamino
- preparing
- cooh
- aminobensyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
7203125-5 leg eg éwom-o-è/SWJ/ciä I I i ll. 7203125-5 leg eg éwom-o-è / SWJ / ciä I I i ll.
' I I 'Pms co-N-cfi---,--coo med 6-aminokapronsyra med formeln NH-_ ___ 2 (CHQ 5 cooH III och att reaktionsprodukten om så önskas överförs till ett salt.Pm co-N-c fi ---, - coo with 6-aminocaproic acid of the formula NH-_ ___ 2 (CHQ 5 cooH III and that the reaction product is transferred to a salt if desired.
Omsättningen av ampicillin med 6-aminokapronsyra utförs lämpligen i vattenhaltigt-alkaliskt medium. Reaktionstemperaturen uppgår företrädesvis till 5 _ 3o°c. 6-(a-aminobensyl-a-penicilloylamino)-kapronsyra och dess farmaceutískt godtagbara salter kan användas för häming av aller- giska reaktioner, som uppträder vid tillförsel av penicilliner.The reaction of ampicillin with 6-aminocaproic acid is conveniently carried out in aqueous-alkaline medium. The reaction temperature is preferably 3 to 30 ° C. 6- (α-aminobenzyl-α-penicilloylamino) -caproic acid and its pharmaceutically acceptable salts can be used to inhibit allergic reactions which occur upon administration of penicillins.
Sålunda kan in vitro utfällningen av anti-penicilloyl-anti- kroppar, framför allt anti-ampicilloyl-antikroppar (utvunna ur kanin- och marsvinssera), genom penicilloylëantigener hämmas medelst 6-(a-aminobensyl-a-penicilloylamino)-kapronsyra. Det har vidare visat sig, att det ovannämda penicilloinsyraderivatet hämmar hemagglutinationen av med anti-penicilloyl-antikroppar, framför allt anti-ampicilloyl-antikroppar, förinkuberade erytrocyter genom ampicilloyl-antigener. Likaså låter sig den genom ampicilloy1-anti- gener framkallade kontraktionen av det medelst anti-ampicilloyl- -kanin-Yßglobulin passivt sensibiliserade marsvinsileumet (Schultz- Dale-försök) hämmas. In vivo kan penicillinallergiska reaktioner såsom exempelvis passiv hudanafylaksi hos marsvin och urticariell hudreaktion hos ampicíllinallergíska människor hämmas genom 6-(a- -aminobensyl-a-penicilloylamino)-kapronsyra. 6-(a-aminobensyl-a-penicilloylamino)-kapronsyra och salter _ därav kan användas i fonn av farmaceutiska preparat, vilka innehåller föreningen eller dess salter i blandning med ett för enteral eller parenteral applikation lämpligt, farmaceutiskt, organiskt eller oorganiskt, inert bärarmaterial, t.ex. vatten, växtoljor, polyalkyler glykoler osv. De farmaceutiska preparaten kan föreligga som exempel- 7203125-5 vis lösningar, suspensioner eller emulsioner. De kan eventuellt också vara steriliserade och/eller innehålla tillsatssubstanser såsom konserverings-, stabiliserings-, vät- eller emulgermedel, salter för förändring av det osmotiska trycket eller buffert- substanser. De kan även innehålla andra terapeutiskt värdefulla substanser.Thus, in vitro the precipitation of anti-penicilloyl antibodies, in particular anti-ampicilloyl antibodies (derived from rabbit and guinea pig sera), can be inhibited by penicilloylene antigens by 6- (α-aminobenzyl-α-penicilloylamino) -caproic acid. It has further been found that the above penicilloic acid derivative inhibits hemagglutination with anti-penicilloyl antibodies, especially anti-ampicilloyl antibodies, preincubated erythrocytes by ampicilloyl antigens. Similarly, the contraction of the ampicilloy1 antigen-induced contraction of the guinea pig silage passively sensitized by anti-ampicilloyl-rabbit Yßglobulin (Schultz-Dale trial) can be inhibited. In vivo, penicillin allergic reactions such as, for example, passive skin anaphylaxis in guinea pigs and urticarial skin reaction in ampicillin allergic humans may be inhibited by 6- (α-aminobenzyl-α-penicilloylamino) -caproic acid. 6- (α-Aminobenzyl-α-penicilloylamino) -caproic acid and salts thereof can be used in the form of pharmaceutical preparations which contain the compound or its salts in admixture with a pharmaceutically, organically or inorganic inert carrier material suitable for enteral or parenteral application. , e.g. water, vegetable oils, polyalkyls glycols, etc. The pharmaceutical preparations may be present as exemplary solutions, suspensions or emulsions. They may also be sterilized and / or contain additives such as preservatives, stabilizers, wetting or emulsifying agents, salts for altering the osmotic pressure or buffering substances. They may also contain other therapeutically valuable substances.
För oral terapi konmer doseringar från 200 - 600 mg per medi- kation i betraktande. Sådana doseringar kan tillföras två till fyra gånger dagligen.For oral therapy, dosages ranging from 200 to 600 mg per medication are considered. Such dosages can be administered two to four times daily.
Uppfinningen belyses närmare i följande speciella utförings- exempel, i vilka förekommande temperaturuppgifter är angivna i Celsius-grader. ' Exemgel 1 _ 26 g 6-aminokapronsyra i 345 ml 1,0 N natronlut försätts under minuter med 58 g ampicillin-trihydrat vid 100 och omrörs i ytterligare 20 minuter, varpå lösningen hälls på 1 kg "Amberlite IR 120" och elueras med vatten. Vattenlösningen lyofiliseras, àtera stoden löses i alkohol och fälls med etylacetat. Det utfällda materialet omsätts i metanolisk lösning med 2N natriumetylkaproat i etylacetat och fälls med eter. Ur metanol/eter får man efter behandling med djurkol natriumsaltet av 6-(a-aminobensyl-a-penicil- loylamino)-kapronsyra; smp. 157-1600, [a]š5 = +30,3° (1,0 i vatten).The invention is further elucidated in the following special embodiments, in which existing temperature data are given in degrees Celsius. Example gel 1 - 26 g of 6-aminocaproic acid in 345 ml of 1.0 N sodium hydroxide solution are added for minutes with 58 g of ampicillin trihydrate at 100 and stirred for a further 20 minutes, then the solution is poured onto 1 kg of "Amberlite IR 120" and eluted with water. . The aqueous solution is lyophilized, the atheroscope is dissolved in alcohol and precipitated with ethyl acetate. The precipitated material is reacted in methanolic solution with 2N sodium ethyl caproate in ethyl acetate and precipitated with ether. After treatment with animal charcoal, the sodium salt of 6- (α-aminobenzyl-α-penicilloylamino) -caproic acid is obtained from methanol / ether; m.p. 157-1600, [α] D 25 = + 30.3 ° (1.0 in water).
Exemgel 2 En kapsel för oral tillförsel innehåller följande komponenter: 6-(a-aminobensyl-a-penicilloylamino)-V kapronsyra-natrium 200 mg mjölksocker 70 mg magnesiumstearat 3 mg talk g 17 mgExample 2 A capsule for oral administration contains the following components: 6- (α-aminobenzyl-α-penicilloylamino) -V caproic acid sodium 200 mg lactose 70 mg magnesium stearate 3 mg talc g 17 mg
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH355871 | 1971-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE406198B true SE406198B (en) | 1979-01-29 |
Family
ID=4258572
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7203125A SE406198B (en) | 1971-03-11 | 1972-03-10 | METHOD OF PREPARING 6- (ALFA-AMINOBENSYL-ALFA-PENICILLOYLAMINO) -CAPRONIC ACID |
| SE7513807A SE7513807L (en) | 1971-03-11 | 1975-12-08 | PENICILLOIN ACID DERIVATIVE |
| SE7514031A SE7514031L (en) | 1971-03-11 | 1975-12-11 | PHARMACEUTICALS |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7513807A SE7513807L (en) | 1971-03-11 | 1975-12-08 | PENICILLOIN ACID DERIVATIVE |
| SE7514031A SE7514031L (en) | 1971-03-11 | 1975-12-11 | PHARMACEUTICALS |
Country Status (21)
| Country | Link |
|---|---|
| AT (2) | AT312802B (en) |
| AU (1) | AU461136B2 (en) |
| BE (2) | BE780471A (en) |
| CA (1) | CA972759A (en) |
| CH (1) | CH546783A (en) |
| DE (2) | DE2211420A1 (en) |
| DK (1) | DK136977B (en) |
| ES (2) | ES400624A1 (en) |
| FI (1) | FI52345C (en) |
| FR (2) | FR2128824B1 (en) |
| GB (2) | GB1322149A (en) |
| HK (1) | HK14676A (en) |
| HU (2) | HU165203B (en) |
| IE (2) | IE36203B1 (en) |
| IL (2) | IL38865A (en) |
| NL (2) | NL7202771A (en) |
| NO (1) | NO138142C (en) |
| PH (2) | PH12264A (en) |
| SE (3) | SE406198B (en) |
| YU (1) | YU35011B (en) |
| ZA (2) | ZA721363B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4316882A (en) * | 1978-04-20 | 1982-02-23 | Levine Bernard B | Compositions for testing to predict and/or diagnose allergy to penicillins |
| CA1209477A (en) * | 1981-03-26 | 1986-08-12 | Bruce E. Haeger | Composition of matter comprising a lyophilized preparation of a penicillin derivative |
-
1971
- 1971-03-11 CH CH355871A patent/CH546783A/en not_active IP Right Cessation
-
1972
- 1972-03-01 ZA ZA721363A patent/ZA721363B/en unknown
- 1972-03-01 IL IL38865A patent/IL38865A/en unknown
- 1972-03-01 IL IL38864A patent/IL38864A/en unknown
- 1972-03-01 ZA ZA721364A patent/ZA721364B/en unknown
- 1972-03-02 NL NL7202771A patent/NL7202771A/xx not_active Application Discontinuation
- 1972-03-02 AU AU39571/72A patent/AU461136B2/en not_active Expired
- 1972-03-02 NL NL7202772A patent/NL7202772A/xx unknown
- 1972-03-02 PH PH13316A patent/PH12264A/en unknown
- 1972-03-03 PH PH13315*UA patent/PH9295A/en unknown
- 1972-03-06 CA CA136,277A patent/CA972759A/en not_active Expired
- 1972-03-07 IE IE281/72A patent/IE36203B1/en unknown
- 1972-03-07 IE IE282/72A patent/IE36204B1/en unknown
- 1972-03-07 AT AT188772A patent/AT312802B/en not_active IP Right Cessation
- 1972-03-07 AT AT188672A patent/AT331389B/en not_active IP Right Cessation
- 1972-03-08 FI FI720618A patent/FI52345C/en active
- 1972-03-09 DE DE19722211420 patent/DE2211420A1/en active Pending
- 1972-03-09 DE DE19722211419 patent/DE2211419A1/en active Pending
- 1972-03-10 HU HUHO1460A patent/HU165203B/hu unknown
- 1972-03-10 YU YU625/72A patent/YU35011B/en unknown
- 1972-03-10 ES ES400624A patent/ES400624A1/en not_active Expired
- 1972-03-10 SE SE7203125A patent/SE406198B/en unknown
- 1972-03-10 FR FR7208435A patent/FR2128824B1/fr not_active Expired
- 1972-03-10 GB GB1135172A patent/GB1322149A/en not_active Expired
- 1972-03-10 GB GB1135272A patent/GB1333524A/en not_active Expired
- 1972-03-10 HU HUHO1459A patent/HU166712B/hu unknown
- 1972-03-10 DK DK112072AA patent/DK136977B/en unknown
- 1972-03-10 BE BE780471A patent/BE780471A/en unknown
- 1972-03-10 FR FR7208434A patent/FR2128823B1/fr not_active Expired
- 1972-03-10 ES ES400623A patent/ES400623A1/en not_active Expired
- 1972-03-10 BE BE780472A patent/BE780472A/en unknown
- 1972-03-10 NO NO790/72A patent/NO138142C/en unknown
-
1975
- 1975-12-08 SE SE7513807A patent/SE7513807L/en unknown
- 1975-12-11 SE SE7514031A patent/SE7514031L/en unknown
-
1976
- 1976-03-18 HK HK146/76*UA patent/HK14676A/en unknown
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